


The Third Time

by QuarterToFour



Category: Supergirl (TV 2015)
Genre: F/F, F/M, Inspired by Maren Morris's 'Hero' album, Winn & Lena are my brotp headcanon, Written on a SuperCorp slant but Karamel is cannon throughout, this fic is ANTI MON-EL fair warning to Karamel shippers
Language: English
Status: Completed
Published: 2017-05-19
Updated: 2017-09-12
Packaged: 2018-11-02 13:41:00
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 10,885
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10945662
Author URL: https://archiveofourown.org/users/QuarterToFour/pseuds/QuarterToFour
Summary: Winn goes for the gold in the superfriend category.Winn loved Kara Danvers. Loved her a lot. He thought she was kind, passionate, and beautiful. He’d once been in love with her too, but Kara hadn't returned his feelings and it hurt like hell to watch her fall for James instead of him. He ignored Kara for a few days and sulked with a six pack of beer in front of his tv. Then he pulled his big boy pants up over his geeky ass and accepted that if friendship was all Kara felt for him than that’s what he would take and he’d like it too. Winslow Schott Jr. might be a shy, nerdy, gamer, techie, mad sewing skills never gets the girl sort of guy, but he was not that asshole who wouldn't take no for an answer.





	1. The Time(s) when Mon-El was an all around A-hole

**Author's Note:**

> Canon until S2E16 "Starcrossed".
> 
> Winn is my favorite Supergirl character and given his leap to emotional maturity between this season and the last, he's been criminally underused as a character. This fic was inspired by Winn's speech to James ('We're here to give information!') upon making the Guardian connection.
> 
> I was so impressed at how the tables turned. Winn was now the guy who accepted his place in the background, yet understood his role was important and James was the whiny man-baby missing the spotlight. Stark contrast from season 1. 
> 
> I wanted to write Winn's journey from Kara's whiny, lovable little bro to awesome dude with a good sense of self who has managed to maintain one of the healthiest, supportive, romantic relationships on this show. (Shout out to Sanvers!) 
> 
> This was originally supposed to be about the Winn-James-and Kara in the Middle relaish, but idk, Lena Luthor met Winn under a table with a black body generator between them and my Brotp headcanon got in the way. 
> 
> And Karamel is here too. But it's Anti Mon-El. VERY ANTI MON-EL. 
> 
> But this fic is really all about Winn. 
> 
> With those explanations/disclaimers in mind, happy reading!

Winn loved Kara Danvers. Loved her a lot. He thought she was kind, passionate, and beautiful. He’d once been in love with her too, but Kara hadn't returned his feelings and it hurt like hell to watch her fall for James instead of him. He ignored Kara for a few days and sulked with a six pack of beer in front of his tv. Then he pulled his big boy pants up over his geeky ass and accepted that if friendship was all Kara felt for him than that’s what he would take and he’d like it too. Winslow Schott Jr. might be a shy, nerdy, gamer, techie, mad sewing skills never gets the girl sort of guy, but he was not _that_ asshole who wouldn't take no for an answer.

So he’d slipped back into his role of supportive best friend, and got used to being the moon to Alex’s sun, in Kara’s life. She’d always go to Alex first, but Winn could live with being second – would be happy with second – if it meant Kara knew she could always count on him. She did.   
She showed it in the little things. _How_ _are you?_ texts, at 2:33 pm for no other reason just to hear his answer, and pizza knishes from his favorite joint in Gotham that showed up on his desk in the DEO accompanied by a _scribbled :)_ _Don’t_ _share (w Alex!)_ sticky note on the anniversary of his father’s imprisonment. His feelings of unrequited love had suffocated quietly in the face of Kara’s gratitude and pure relief that Winn’s friendship was still on the table.

Kara broke up with James because she couldn’t be Kara Danvers the reporter, National City’s superhero and James Olsen’s Girlfriend all at once. Winn heard about it and his heart jolted a bit like it went over a speed bump, but he’s still not _that_ asshole, so he shut down hope and tried to be there for both of them. Things stabilized between the super friends although Winn hung out with James a lot less now that they don’t share the same place of employment.

That changed when James roped him into being tech support on the Gaurdian gig. He works with Kara during the day and with James and night and tech support is awesome. Of course, Kara found out because keeping a secret from the rest of the gang is like trying to keep bears from honey. Tech support is less awesome for a bit, but Kara got over herself eventually.

In the middle of all this, Mon-El of Daxam showed up and monopolized The DEO’s energies with helping him acclimate to Earth. Winn liked Mon-El then. He was fun, in an I’m new here so let's shoot the shit, damn the consequences, kind of way. Winn had got to show Mon-El what a good time on Earth looked like, before he’d found out that Daxam’s good time was similar, plus y’know, sex slaves. Which explained why Mon-El was so good at darts. So he and Mon-El were bros for a hot minute and it was cool, and he liked him. Then Mon-El announced that Kara like-liked him (well, he said they’d banged and Kara didn't seem the type for casual sex if her reaction to catching him and Siobhan mid coitus in the CatCo supply closet was anything to go by.) and because he loved Kara Danvers like she loved potstickers, he’d smiled and said he was happy for her, and liked Mon-El a little less.

If he and James ditched Gaurdian duty that night and met up to punch cars really hard, it's not like anybody (Kara) ever has to know.

And then he’d met Lyra and opened up to the chance to be someone’s sun, moon and earth all at once. The honeymoon phase lasted three weeks. Three amazing weeks, in which he learned that Lyra’s favorite thing about earth was micro brewed beer and that she loved The Sound of Music and hated peanut butter and was allergic to shellfish. He’d told her about his love for Star Wars and she said she already saw all the films and yes, the original trilogy was perfect and the prequel trilogy was shit, so they’d binge watched the fourth season of Orphan Black and she’d taught him how to throw a knife like Helena. Tried to, anyway.

The honeymoon ended abruptly when he broke into the National City Institute of Art, had sex with his alien girlfriend in front of ‘The Scream’ painting and got hauled out of bed by Maggie Sawyer to watch a video of him stumbling around in front of an uberexpensive painting that’s hanging on the wall in one frame and gone the next. Lyra is nowhere in that video and he only got to leave because Alex pulled the _I’m_ _your_ _girlfriend_ , _give_ _me_ _benefits_ card with Maggie.

Kara spared a minute from whatever was happening between her and Mon-El, (he’s actually the Daxam heir? Mom and Dad want him back and it's alien Romeo and Juliet? He’d overheard Vasquez making that analogy to J’onn but he couldn't exactly focus on Kara’s relationship status cause his girlgriend was AWOL with a Van Gogh.) to tell him Lyra’s not where she should be because Valerians can't be seen by cameras.

He found Lyra in a trailer park. _You were a mark_ Lyra told him. He finally dragged the truth out of her and it was a little too nerve wracking in his I’m- the- guy- who- stays-in-the-van’s opinion, but _“You were different.”_ , and the look on Lyra’s face when she hugged her little brother made Winn decide Lyra was worth another shot.

He was so pleased and caught up in this revelation that when Kara came to him for a second opinion about her Mon-El problems he doesn't stop to think how their situations might have been different. Lying for your little brother who’s being held hostage, and lying out of cowardice and a past you want to hide in order to get the girl are two very different things. Hindsight will be 20/20 but, right then he made like Alex, and he blurted some platitude about lying for the right reasons, but Kara broke up with Mon-El anyway.

In an unforeseen weakness to DEO security measures, prisoners are not tested for psychic powers before being let through public areas and Kara was forced into a musical dream coma by the Music Meister and a jaunt to Earth 1 to visit Team Flash happened. They said they would fix it, but Barry fell to the same coma.

Lena Luthor of all people texted him. _This is Lena Luthor. I heard through the grapevine Kara lost her job. She’s not at home or picking up her phone. Is she ok?_ Winn hadn’t known Kara had been fired, but he couldn’t tell that to the L-Corp CEO, nor could he tell her that Kara Sunshine Danvers, former CatCo reporter was actually a comatose Supergirl just then. He riffed off her own message and replied, _She was really down about it and Alex sent her on a no-phones trip to to an elephant farm in Kenya. How did you get my number?_ Lena hadn’t sent a reply, but when he'd checked his personal email, there had been a polite message from Jessica.Huang@L-Corp.com informing him that corporate espionage is illegal and that any attempt to reopen his backdoor into L-Corp’s network would result in prosecution to the fullest extent of the law. He thanked his lucky stars he’d used his personal computers for the hack. If he’d given a Luthor access to the DEO servers J’onn and Alex would’ve killed him before Kara had a chance to intervene.

An exhausted Kara came back from Earth 1, and there was screams of joy, (Winn) a few hidden tears of relief (Alex, J’onn), a gruff ‘ _glad you’re back, Little Danvers_ ’ (Maggie), a ‘ _Kara_ _and I are back together_ ’ announcement (Mon-El) and a muttered ‘What the fuck you thinking taking up with Daxamite Douche, girl’ (Vasquez) is drowned by the the noise.

Life went back to normal alien clobbering by day and dating Lyra and ass-kicking with Gaurdian at night. Winn forgot about Lena until Kara had sent him a panicked _ELEPHANT_ _FARM???_ _She_ _wants pictures!?!?_ text while Supergirl had taken a short break to go have lunch with someone.

He’d kicked himself for forgetting and he and Lyra had a blast photoshopping Kara into as many adorable poses as possible on the wrinkled, grey beasts.Mon-El stopped by while they were doing their frantic last minute editing to raid his Pringles drawer, and asked if Winn could edit Kara into lying on the elephant’s head in lingerie and the elephant’s trunk – Lyra had threatened to choke him with the stupid elephant trunk if he finished that sentence and Mon-El had left the apartment with all of his Pringles cans. Even the mustard ones.

For just a second, Winn hoped he’d choke on them.

Lena Luthor, still dressed from work, holding plumerias and pizza, turned up at game night that week. She said Kara invited her. Awkwardness ensued when Kara wasn’t there to confirm because Supergirl was across town putting out a five alarm fire, but Lena obligingly pulled up her text conversation with said invite from Kara. “ _Didn’t know a Luthor_ _was allowed to use heart emojis_ ” Maggie smirked as she invited Lena inside. Lena blushed scarlet and muttered something that Winn couldn't hear over Alex’s hissed instructions to text Kara right _now_ that it better be Kara Danvers with no cape in sight who comes through the apartment door. And that she’d kill her when she got here, but to hurry the fuck up and get here before Luthor got suspicious.

Everyone mutually agreed that Kara was late thanks to an emergency dentist appointment, and Winn made sure to text Kara her own excuse that time. Kara took one look at Lena and forced her into sweats. Lena went quietly and Winn never realized how human the CEO could be until she came out of the bathroom, her hair down in soft waves, wearing Kara's old Midvale High sweater, black leggings and fuzzy, hello kitty sleep socks, looking just a little lost without her Chanel and Prada armor.

It got awkward again when Mon-El and Kara had a mini fight over who Kara was supposed to partner with for the games. _It’s_ _Lena’s first game night!_ She’d said.

 _And I’m your boyfriend_. he'd shot back. Kara stood in the middle of the room and looked like a helpless puppy, and Mon-El had looked petulant, and Lena had seemed on the verge of making her excuses and leaving.   
  
It was Lyra, also new to game night, and the only well-adjusted alien in the room, who solved the tension by asking Lena if she wanted to join Team Linn for the night. (The name fits!) Lena had accepted and Kara partnered with Mon-El.

James was with Lucy, who was in town for the weekend, and Maggie with Alex for a total of 4 teams. For the first time ever, Winn found himself on the winning team for game night as Lena slayed everyone in Trivial Pursuit and Texas Hold Em. (Girl had a poker face of stone, even Alex admitted it.)

Lyra brought in the win on Operation. _It’s_ _like_ _picking_ _handcuff_ _locks_ , she’d said, winking at Maggie.

Of course Maggie had demanded a demonstration, and Lyra showed off her Houdini skills to the gang. Then they’d moved on to video games and Winn had beat his own previous record for Rainbow Road. When Kara had declared Team Linn the winners of game night, he’d kissed Lyra so enthusiastically, even Maggie had blushed. Lena had smiled like Kara had said magic was real, and _oh_ , Winn knew that look. His traitor heart had panged in empathy, but Kara was happy with Mon-El and who Kara was with was none of his damn business, and y’know, Winslow Schott Jr. was not _that_ asshole who mixed in with his former crush’s relationships.

The pizza and beer had finally been delivered then, and after everyone was comfortably buzzed the real fun started. James and Lucy had sprawled themselves over the couch in a way that made Winn suspect that Lucy was back in town _because_ of James, and Winn was happy for him.

Lyra was telling Maggie and Alex about her arrival on Earth and they were questioning her about how she thought it best to avoid what all three of them call “ _ **The**_ _**Great Alien Fiasco of 2003**_ ”. From the overusage of the word _goo_ in the conversation, Winn didn't think he wanted details of that particular story, so he’d bussed Lyra on the temple and turned to the other side of the room to join Mon-El, Kara and Lena.

Lena looked really uncomfortable again, because she and Kara were talking about Kara’s job prospects, but MoN-El’s constant interruptions about working from home made it clear to everyone in that conversation how the Daxamite expected his night to end. Kara’s face was so red, Winn half-expected it to explode in flames.

Winn casually theorized to Lena a couple of ways to make a telelens that could record Valerians, and Lena grabbed onto the topic with both hands. Kara gave Winn an incredibly grateful look and spent the rest of the night talking to Mon-El while wearing, what Winn later named her _rather_ _be_ _talking_ to Lena face, and stuffing her face with pizza.

  
The night had ended on a high note with Winn securing an invite to L-Corp to discuss design plans for the telelens, and Lucy and Lena got high enough to let the walls down and recount the time when Little Luthor and Little Lane had concocted a Valentine’s Day scheme and gotten Lex, Clark and Lois into a love triangle using notes slipped into each of the three’s lockers at school. The fallout had been catastrophic. The trio hadn't spoken to each other for a month. _You little shits!_ James growled. _That month was torture! I was like Hermione in the Goblet of Fire trying to stay friends with all of them at once!_ Lena and Lucy had cackled hysterically at that.

  
Maggie and Alex were the first to leave, and James and Lucy followed them out quickly. After collecting a few of the empty pizza boxes to throw into the hallway incinerator on their way out, Winn and Lyra had thanked Kara, and Lyra said something about defending their win next week. Kara and Mon-El had both made weird hand motions automatically. Lyra made it back using both hands, and a smirk on her face.

They finally left as Mon-El tapped Kara on the ass and headed for her bedroom with a _see you soon,_ _babe_ , and Lena came out of the bathroom in her dress again, and started collecting the beer bottles and Twerpz pieces scattered on the couch and floor. The last thing Winn had seen before shutting the apartment door was Lena Luthor in a $5000 dress and bare feet, handing Kara a used wineglass with a _“I had an amazing time_ _tonight,_ _Kara_.” And Kara had given her the smile that was once James-Olsen-Only, and responded with a soft, relieved, _“Good.”_

 


	2. The Time When Lena Cried and Mon-El Fucked Up

**Summary for the Chapter:**

> When Kara had to step out, Winn stepped in. Winn & Lena bonding time. Car smashing is an acceptable bonding time activity.

**Notes for the Chapter:**

> Anyone know the proper name for Lyra's species? I thought it was Valerian, now I'm realizing that might be from GOT.

The next few weeks went by quickly. The DEO underwent upheaval with the bounty out on Supergirl. Winn barely had time to breathe between scanning the city for traces of Kryptonite, and busting Supergirl bounty hunter hopefuls with Gaurdian at night.

Lena officially found out about Kara Danvers’s alt-identity when a bullet had bounced off Kara’s chest, tearing open her shirt to reveal the famous ‘S’ symbol of National City’s superhero.

According to what Alex recounted to him, that was when Kara had begun her usual rambling, litany of excuses, but Lena had merely lifted her hand to pause the word vomit and asked Kara to give her some credit for intelligence, and to give her (verbatim quote, Schott) _a week to process that my two best friends are actually the same liar._

Kara had been a bumbling mess for the next two days. She barely managed to hold up a measurement of authority while taking out criminals and without her CatCo job to fill her time off from Supergirl, she’d practically glued herself to her couch with a mix of tears and cheetos crumbs. Things had come to a head when Mon-El entered Kara's apartment to announce that Kara was going to fly him to Vegas where they’d do some high roller gambling, win a ton of cash, and forget all about Lena Luthor’s ungrateful ass.

 

Kara had made a noise between a laugh, and a sob. _I lied to her, Mon-El! For months! She’s not ungrateful for being upset about it, and I trusted her from the moment she saved this city from Medusa, so I have no explanation for not telling her other then me being selfish, selfish,selfish! She doesn't have to forgive me for being selfish!_

 _Why not, babe?_ He countered earnestly. _You forgave me._ Then he’d leaned in to kiss her, and Kara hadn't said anything, and let him.

Winn only knew about this exchange thanks to Lyra, who had dropped by to ask Kara what Winn’s favorite vacation activity was. (Apparently, a trip to the Metropolis’s Gamer Association was in his future. He lov- _liked_ -he really liked his girlfriend.) Winn found himself pissed to the nth degree. He wasn't sure if it was at Lena, or Mon-El,or Kara, or all three.

So if he’d hacked L-Corp again, _corporate espionage laws be damned_ , and located a single email address from a list of company employees and if an email with the subject _21 reasons why my Kryptonian friend didn't tell me she was Supergirl_ , appeared in a certain raven-haired CEO’s inbox, it's not like anybody, (Kara) ever had to know about it.

He’ll probably never know if it was him, or Kara, or someone else, all he knew at next game night was that Team Linn had its third member back and they whooped ass on their last lap of Bowser’s Castle. A bouquet of plumerias took up half the counter behind them, and Kara’s smile didn't falter once. Not even when Mon-El ate the last potsticker.

 

It was deep into summer when James, in a brilliant back-room maneuver, used the fallout that was CatCo bungling the reporting of a major celebrity scandal, to oust Snapper Carr from his top dog position within the Media department of CatCo, demoting him to head copy editor.

After a thorough humiliation by his replacement, something most of the CatCo employees quietly delighted in, Snapper Carr resigned from CatCo. With a non-compete clause from CatCo firmly in place, he took a job in the L-Corp mailroom. That had been Kara's doing.

James had offered Kara her job back immediately, and Kara had hugged him so tight, Lucy had gone jealous girlfriend like the days of yore for a moment. They had thrown a massive party in Kara’s apartment to celebrate. James was the guest of honor, but Winn had spotted him grabbing Lena and Lucy for a private toast in the corner and it had clicked neatly. Lena for the money to create a scandal, Lucy to collar him with the non-compete and James to boot him. The Three Musketeers.

Winn briefly considered hacking L-Corp to find out exactly how much Lena Luthor had paid to engineer a scandal big enough to sink Snapper Carr, but decided against it. If Lena didn't want Kara to know of her involvement then Winn would keep it quiet. Also, things were going in the _let’s_ _move in together_ direction with Lyra and a jail cell as his permanent place of residence might put a kink in that. Kara was thrilled, and Winn left it at that.

Winn got so busy with his DEO job, his telelens project he'd been drawing designs for on the side, and picking out furniture for his new apartment with Lyra in his spare moments, he almost forgot to get his funk on when the Toyman Tradgedy bubbled up to front and center in the news. He’d been rudely reminded when he'd gone to grab a coffee from the food truck near his apartment and his father’s maniac grin had been plastered across the cover of every newspaper. Even the ones Weed Guy used to hide the drugs in. (Drugs he'd brought. Just that once.)

Kara hadn't forgotten though. A flat out full turkey dinner, neatly packaged for reheating, of Thanksgiving proportions was waiting for him on his desk. Kara had scribbled, _Share with Lyra tonight. I made James promise Gaurdian and Co. are off duty tonight. Love you!_

Kara had been so busy lately. She was working her ass off to get earn a promotion to Junior Reporter, (she’d refused James offer to reinstate her at her old position, fearing he’d be accused of nepotism.) and she superheroed the hell out of every other waking moment. Winn was more familiar with the back of her head than her Sunny D smile just then, but she’d remembered. It meant the world to him and he texted her so. He got a text back, _yo man. Dis Mon-El. If there's any extras can you drop em off? Kara didn't buy for me_ , which he ignored. The Daxamite could get his own food.

  
Winn had cried his daddy issues out on Lyra’s shoulder and they’re cuddled on the couch, passing a joint made from his morning purchase back and forth, when Mon-El had breezed in. He cleared their left overs spread out across Winn's kitchen counter into a bag and left with a casual, _Thanks, man. Anytime you want something better than that crap your smoking, I got your back._

Winn had been arguing with Lyra about leather couches vs. bean bags in the living room. (Lyra had won when she pointed out that Netflix and Chill could only happen on one of those things. Winn humbly apologized to all men he had mentally accused of thinking with their dick and ordered the fucking fifteen hundred dollar couch.) He’d been distracted at the time, so it only occurred to him to wonder how exactly Supergirl’s boyfriend had a hookup to anything drug related much later.

_Like five months later._

During those five months Winn accepted Lena’s invite to L-Corp, and Jess reworked Lena’s schedule ten times to accommodate their bi-monthly meetings.

Jess had waved away his apologies _. It's her down-time, Winnie. I haven't seen her put on a lab coat since Lex was arrested, and lord knows she needs more down time spent with people who talk nerd, and not unrequited crushes in sunshine form. Don't tell her I said that._

He’d nodded. _Wouldn't even know where to start that awkward conversation._

 _You start it, I'll bury you_. Jess had replied as she printed him out his appointment schedule.  
_Here’s your schedule and if I have to rework it, because you don't have your shit together I will be very, very unhappy._

He’d kept his shit together, because if rumors be true, facing down Supergirl’s heat vision would be preferable too dealing with unhappy Jess. What was it with assistants to powerful CEO’s?

His original design underwent so many revisions that in the time it takes for Lena to go from _Kara’s super-rich, super-hot, super-intimidating CEO friend_ to _just my awesome friend Lena who can do amazing sciencey things in a lab coat and goggles_ , Winn didn’t recognize his own telelens. The important point was that the damn thing worked, and he and Lena filed for the patent jointly. Lena insisted that it be filed under her name personally, not L-Corp’s, and that Winn take 60% of rights and ownership.

_I'm a billionaire Winn, and this project had nothing to do with my company, and everything to do with you and your brilliant, under appreciated genius. I don't need the money and I know your looking into buying an apartment, among other things, so just…let me do this for a…friend._

Lena had sounded so uncertain about calling Winn a friend, he’d caved immediately, with a _you're an incredible friend to have, Lena Luthor._ Lena had given him a smile like he said L-Corp stocks were up and Lord Tech stocks were down and Winn could practically see the Number of Friends Lena has in National City list in her head tick up to two.

(Jess claims she doesn't count since she works for Lena.)

With his new status as friend cemented, Winn took the liberty of bringing the sushi and champagne ( _when you meet with a girl, eat like a girl._ Lyra had grilled that one into him the first time he'd ordered a burger with the works and she'd wound up eating half his fries.) to their last scheduled appointment.

Jess had seemed hesitant to let him through, but he pointed out that he'd kept his shit together as requested, and it was his last official appointment so could she please let him through so that he and Lena could _celebrate their technological genius, baby!_ Jess had let him through, and the minute he got in there, the first thing he saw was a box of caramel filled cupcakes from that store Cat Grant ordered from, and had threatened to behead the foolish idiot who would dare to eat one while her back was turned. The box had Kara’s handwriting scrawled on it in purple, glittery marker, _Keep your head up today, Lena. Family fights for each other. Always. –Kara._

Lena had been slumped behind her office desk, a tumbler of scotch at her elbow, a cupcake on a napkin in front of her, biting her lip and staring at her television that was blaring out coverage of Lex Luthor’s trial that had wrapped today, two years ago. _Shit. He’d forgotten about Lex._

  
Winn wanted to back out of the room, but it was too late. Lena had already spotted him. Her posture had straightened, and her face smoothed into a mask of cool politeness. Winn had marveled at how fast she recovered her composure. Had he not seen her a few moments before he would have thought today was any other day for Lena Luthor, HBIC CEO.

 _Winn,_ she greeted him. _You here for my signature on the final papers?_ He'd nodded and produced said papers, setting the sushi and champagne on her desk. She’d looked at the party food like it was snow in Miami. She signed the papers quickly and then handed him back the pen. _Thank you, Winn. It's been a pleasure to collaborate with someone so bright on such a promising invention._

 _I forgot about, Lex._ He interrupted _. And I’m sorry and I know you’re hurting even though you’re trying to pretend that you’re not…_

 _I don't know what you’re talking about, Mr. Schott._ Lena had cut in, hand inching towards the call button on her desk. _We’ve concluded our scheduled business for today, so if that will be all?_

_Winslow Schott Jr., Lena. You're talking to the son of the Toyman. I know you're shit at this, because you’re not used to having people who care, but I care about you. I care about you because, um, you’re my friend and a much better person than you give yourself credit for, and I know you send flowers to every single one of Lex’s victims’ families every year, even though you get back hate mail for it, it's like, the least encrypted piece of info on the L-Corp servers. So drop the ice bitch routine. I really don't know what to do with crying women, that’s more Kara’s department, but damnit, Lena, I'm opening this sushi and we're putting food into you. And if you need to cry over your shitty family, then cry because Lord knows I've soaked through Kara and Lyra's shirts a few times over shitty family members myself._

_Luthor’s_ _don't_ _cry, Mr. Schott._ Lena told him. _Bullshit_. He'd said back, nearly slicing his finger open on the hard plastic encasing the spider roll he was trying to open. He’d yanked at the tape a couple times, and Lena pulled a pair of scissors seemingly out of thin air and handed them to him.

 _We’re eating on the couch_ , she'd said standing and coming around her desk to open the rest of the packages while he struggled with the first.

She'd toed off her heels and headed to the couch. Her shoulders dropped as she walked, but otherwise she maintained remarkable self-control given that the commentator on TV had just segued into a laundry list of Lena’s ‘public displays of prejudice against the alien community.’

Then Winn had stuck his foot so far down his throat it should've split the seat of his pants. _Where’s Kara?_ he'd asked around a precariously balanced stack of sushi containers. _I mean, I know she was here cuz bringing people food on days the world remembers how fucked up their family members are is kinda her thing, and I see she brought you those cupcakes Cat Grant would kill for, but I dunno…she said today was like a day off and unless Livewire or Barry Allen showed up, Supergirl was unavailable. She wouldn't tell the DEO why, but J’onn was wierdly cool with it and now I'm figuring that she took the day off to spend with you to keep your mind off Lex and stuff, which I'm so sorry for forgetting about by the way, but you’re here and the cupcakes are here and Kara wouldn't leave you unless something important came up…_

He'd trailed off when he saw Lena’s gaze flick to the cupcakes and back to him and then her face twisted oddly, and she'd swallowed hard. _She was here._ She said huskily _. But Mon-El…something happened and she said she had to go to him. I mean he’s her boyfriend and I'm just –_

Winn had set the sushi down in front of Lena and shoved a fork in her hand. _You’re just in love with your best friend_ , He’d said plopping down next to and grabbing the remote to shut up the hateful commentary spewing from the TV.

Lena had stiffened into a glass sculpture beside him, and opened her mouth to deny it. The only sound that escaped was the sob that'd been weaving in and out of her voice since he'd walked in, and she pitched forward burying her face in his pale blue shirt.

Lena goddamn Luthor had cried on his shoulder for a total of fifteen seconds. Winn took a perverse sense of pride in that as he'd patted her shoulder awkwardly.

Then Lena had straightened, swiped her fingers under her eyes and speared a piece of sushi with the fork Winn had given her. _Thank you, Winn. She'd said. I trust you will be discrete with this information._

 _Absolutely,_ Winn knew his head did that earnest nod thing that made him look like a bobblehead doll. _If you wanna talk about it to someone who’s been there…_

Lena had given a watery laugh at that _. Why am I not surprised, Mr. Schott?_ She’d asked wryly _._

 _Not sure why I even bothered trying, to be honest._ Winn chuckled back _. With girls like Kara Danvers, Boys like me have an automatic ticket to the friend zone._

Lena’d snorted. _I've met_ _Lyra_ , _Winn_. _Don't sell yourself short._ She’d given him an affectionate punch. _Also, did you insinuate that I'm the sort of girl who gets friend zoned?_

Winn had choked on a piece of sushi and practically fell off the couch in his haste to reassure Lena that's not what he meant.

 _Relax, Winnie._ She told him. _It is true._ Then she’d turned introspective. _Lena Luthor: Friendzoned. It'd make a great tabloid story. Me and my money pining over the cure for vitamin D deficiency in human form._ The joke had been kinda ruined by the sob creeping back into her voice, and despite the ego boost factor Winn wasn't sure he could've handled a double dose of Lena Luthor tears.

  
_What're you doing for the rest of_ _the_ _day?_ He'd blurted. Lena had given him a confused stare.

_I'm just planning to work until I fall asleep at my desk, Winn._

Winn’s head had done the bobblehead thing sideways. _Nonono. You wait here. Eat the rest of the spider roll._ He’d shoved the container into Lena’s hands and went to find Jess.

Winn had never seen Jess so thrilled about canceling her boss’s schedule _. Don't you dare let her come back here today, Winn._ She'd warned him as he bundled Lena into his blue Kia Solo _._

 _Yes, Sir!_ Winn had responded smartly. And then backtracked, _I_ _mean, Ma’am! Yes, Ma'am!_

Jess had rolled her eyes and waved them goodbye as Winn pulled out of the L-Corp underground lot to the sound of Lena’s demands to know where he was taking her or she’d be suing them both for abduction and coercion.

He'd taken her to the junkyard, inducted her into the We-Like- Kara-Danvers-and-She-Likes-Us-But-Not-Like-That and Shitty-Family-Members-‘r-Us clubs simultaneously, and they had picked out a yellow VW Beetle and a black Lexus for each of the clubs respectively. Then Winn had donned his noise canceling headphones, hoisted himself on to the roof of a crumbling Ford Explorer and settled into wait.

The bass line pounding in his ears blocked most of what Lena yelled while punching out the Lexus, but her voice rose considerably when she started in on the Beetle. He'd managed to catch,  _If_   _I had a dime for every time she says deep down he’s a really nice guy, I’d be broke!_ And responded with a grim _Amen!_ while adjusting the volume of his music as high as it could go.

If Lena insisted on pulverizing the shattered, dented, pitiful remains of the Beetle, just the Beetle, before they left the yard, it's not like anyone (Kara) ever had to know.

Winn dropped Lena off at her apartment to assurances that Jack, James, Ben, Jerry and Edy were all waiting for her upstairs. Then he'd checked who had been blowing up his phone the whole ride back. Alex had texted him. Maggie had texted him and he had a missed call from J’onn.

They all said variations of _DEO. NOW._ He had hightailed it there to find Alex jamming guns into her hip and ankle holsters. Maggie was pulling on her arm and trying to calm her.

Alex had looked so out of control, Winn knew immediately that he'd missed a Kara related emergency.

 _What's up, Alex?_ Winn had asked warily.

Alex had jammed the gun in his chest. _Where the fuck were you!?_ She screamed.

 _Alex. Please, Baby, calm down._ Maggie had pleaded. Alex escalated pressure on his sternum and repeated her previous question to Winn.

_Whoa! Ok! I was with Lena Luthor. Please don’t shoot me! Does this freak out ur having have anything to do with why Kara went AWOL on Lena? Lena said it was something to do with Mon-El….?_

_That fucker is dealing!_ Alex yelled and jammed the gun into his chest again. _And I'm gonna murder him, and then if I find out you had an iota of knowledge of what he was doing behind Kara’s back I’ll murder you too!_

Alex had her ANGRY face on and Winn had nearly peed his pants because frankly, Alex intimidated him by just existing, and an Angry Alex was downright terrifying.

 _My sister is bailing that douche bag out of prison right now. With her own savings!_ Alex went off again. The gun had been shoved into his chest so hard, he had toppled onto his ass. Then he’d snapped.

 _Y’know Alex, I don't know everything going on, but right now, Kara needs Supportive Alex. Not this_ \- he waved a hand toward Alex – _raging mess!_

It had taken Alex 30 seconds of meditation on his words, time which Winn spent contemplating that his grandma’s ring really needed polishing _(the fuck, Schott?!?),_ before she finally lowered the gun. _Kara said she’d bring Mon-El to the DEO when she got him out. I'm gonna get her pizza and potstickers so she can eat._

She’d dragged Maggie out with her, who muttered a ragged, but genuine _Thanks_  to Winn as she passed.

Winn had breathed a sigh of relief, rubbed his sore chest and and went to find J’onn.

J’onn had cleared the situation up for him easily. Mon-El was dealing Schmurple.

_It's an alien drug. Only, he’s selling to human children. It causes episodes of disassociative personality disorder, similar to the Dr Jekyll/Mr. Hyde effect. The druggee loses all inhibition and tends to act on his darkest, deepest desires. The drugee usually has no recollection of his actions once the drug wears off._

_So it's like Kara on Red K, but with no memory retention._ Winn offered _. He’s giving this to kids?_

 _Yes_. J’onn confirmed.

Wh _at’s going_ _to_ _happen_ _to_ _him?_ Winn asked. He’d known the answer, but He’d wanted J’onn to say it out loud, make this nightmare for Kara real. If it was real then he could get angry.

_He broke the law, Winn. Federal law, this isn't a petty misdemeanor like trashing a happyhour bar while blind drunk. The DEO handles aliens that are violent threats to humans, or intent on world domination, but thanks to the Alien Amnesty act, aliens are entitled and required to be tried by jury. The DA’s office has been looking into this drug ring for months, and he wants every single person related to this mess in federal penitentiary for the longest sentence he can get._

_So Mon-El is fucked._ Lena had concluded when he’d texted J’onn’s words in to the Team Linn chat.

 _Yeah,_ Winn had agreed and ignored Lyra’s string of smiley emojis she sent him privately.

 _I may be able to call in some favors._ Lena offered.

 _Please don’t._ Lyra responded _. I know you’re thinking of Kara, but one of those human kids on Schmurple bashed on my brother’s best friend’s face with a bat. He had sideswiped the kid’s new, uninsured car the day before. The saddest thing was that when the kid came out of it and realized what he’d done, he cried and called AEMT. Mon-El was distributing drugs that force people to do things that they would never do sober. He deserves everything he gets._

 _Ok._ Lena had sent back _. Has anyone heard from Kara?_

 _Not yet_ , Winn texted.

 _Not yet_ , Lyra texted.

 _How’s_ _Ben and Jerry?_ Winn had asked.

 _Right now I’m favoring Jack_. Lena had responded.

 _Do I need to come over?_ Winn texted.

 _No._ Lena sent back. _I'm being responsible. I'm just sad. Good night._

_Get some sleep, Lena. Keep the TV off._

_Good night, Winn, Lyra._

Winn and Lyra went to sleep after Lena wished them good night and were woken by a banging on their door an hour later. A frazzled Kara had been on the other side. Her eyes were red rimmed and she was wearing a raggedy sweater, sweatpants and the weight of the world around her neck. 

**Notes for the Chapter:**

> No, Schmurple is not canon anywhere. Schmurple is a drink my family made up when I was a kid. Equal parts OJ & grape juice. It is as gross as it sounds, but contains enough sugar to impede rational thinking, so naturally we loved it.
> 
> This is still rambly. Sorry. It's Winn. He makes me ramble. And confuse tenses.


	3. The Time When Mon-El got Evicted, and Winn was the Best Friend on Earth

**Summary for the Chapter:**

> Mon-El mansplains, Alex gets a lead pipe, Maggie gets video, James and Lucy get Drunk, Lena gets the girl and Winn's girl gives him tickets.

**Notes for the Chapter:**

> This is my ramble for Winn.

Winn and Lyra had invited Kara inside, settled her on the couch and asked her how she took her cocoa. Lyra got busy in the kitchen boiling the milk and Winn went to the bedroom, pulled on his _Talk Nerdy to Me_ shirt and panicked.

Kara had been in his apartment for the past five minutes, and he had no idea of what to say to her other then, 'I guess you’ll be partnering with Lena at the next Game Night.' Fucking pathetic.

"Winn," Lyra had said, entering the room and handing him his gym shorts from the floor, "The cocoa’s ready."

"I don't know if I can do this." He'd said to Lyra. "I’m not Alex. I never say the right things and I'm not Alex."

"If she wanted to talk to Alex, she'd be at Alex. Just talk to her Winn. And _listen_. That's important."

Lyra had pecked him on the lips, pulled on her Nikes and left the apartment after telling Kara she was going for a quick run.

Winn had allowed himself to panic for another 30 seconds after the apartment door closed behind Lyra. Then he'd swapped the shorts for his big boy pants, marched into the living room.  
  
He'd sat down on the other end of the couch and picked up his mug. He was casting around for a way to start the conversation, when Kara beat him to it. "I tried to throw Mon-El out." She said flatly.

Winn blinked. "So why are you…" He had trailed off, reluctant to ask, _So why are you here?_. The words seemed so cold.

"He wouldn't leave." Kara said. "He said he had nowhere to go and he needed to sleep. That we’d talk tomorrow about getting him out of punishment. He went to the bedroom and I just couldn't bare the idea of sleeping next to him tonight, or in the same apartment as him."

Her voice cracked and she sipped her cocoa before continuing. "I was afraid he'd accidentally hurt the police if I called them, so I...d'you mind if I sleep on your couch. Just for tonight?" Kara's voice was a whisper.

Winn nodded. "You’re always welcome Kara. You know that."

There’d been the crunch of ceramic and Winn mentally bye - byed the _fucking_ fifteen hundred dollar couch, as his arms had been filled with a crying girl for the second time that day. He patted Kara’s shoulder and let her soak his favorite t-shirt.

When Kara had finally lifted her face, and started apologizing over the spilled cocoa, Winn had waved it away. "It’s ok, Kara. Beanbags were destined for this space anyway."

  
It had taken patience, and a few quiet comments to steer the conversation where he wanted it, but finally, Kara had begun to talk. Her voice had been halting and broken and Winn had desperately ached to hurt Mon-El, the way he had hurt Kara.

Kara had told him how she had taken Mon-El back to her apartment and had asked him the one-word question that had been on everyone's lips since they'd found out the cause for his arrest. _Why?_

Mon-El had obligingly explained his motives.

_"You have to understand Kara that on Daxam a man is expected to look out for himself. Make his own choices. Provide for himself. I didn't have a way of making money, because bar tending and the hero thing you like so much really doesn't pay enough to properly pay for the stuff I need. When I was offered this distributor job it was a lifesaver for me. They paid me a lot of money for something really easy. The way you explained the work system here, there didn't seem to be a lot of jobs like that on Earth, so I took it."_

Winn had nearly upended his cocoa in shock. "He said that? Is he an idiot? He was selling drugs! To children!"

_"Oh, he had an answer for that too." Kara had rasped out, bitterly. He shrugged and said, (Here Kara took on Mon-El’s this-is-my-mansplaining tone.) "On Daxam, taking drugs are consumer’s choice. Adults and children use them to party. You never bothered to tell me it was any different on Earth, so I really don't see why you’re so upset, or why you get to act like I'm some big disappointment."_

Kara had let out another sob and Winn ad wrapped his arms around her and let her cry.

_"I was supposed to make him a hero, Winn. He said he was going to be a hero. He was going to try to be a hero for me. He's not a hero. He's a Daxamite. I was so happy to have someone I couldn't break, I believed in him to a fault and so many people got hurt."_

Not for the first time, Winn had wondered if the tendency to shoulder responsibility for everyone else’s failure was a Super thing, or a Kara thing.

 

"It's my fault." Kara said the words with a conviction of steel and Winn had taken a few breaths to remember exactly what was wrong with selling drugs to children. Mon-El was a smooth, gaslighting douchebag.

Winn thought it was about time he brought up a few points. "Kara, when you first came here, did you know everything about Earth’s customs?" Kara had shook her head.

"When you didn't know Earth policy on things like foisting your work on to the nearest available female and selling drugs to children, what did you do?"

"I asked Alex." Kara said, closing her eyes.

"Right." Winn said. "Why did you ask? Why didn't you just follow whatever you’d done on Krypton?"

"Because," Kara’s eyes snapped opened. "Because it's different here!" She choked out. "And Mon-El doesn't get that. I was an autocrat, Winn. Mon-El was a prince. We were royalty on our planets, but Mon-El refuses to acknowledge that our planets and positions are gone. On this planet we're nothing but ordinary citizens and that spoiled, little prince doesn't want to get it through his head that he is nothing special here. I'm just so done with it, with him. Can I be done, Winn?"

Kara had been a quivering mess begging for someone to tell her that it was ok to drop someone else’s burden, and Winn hadn't wanted to give his permission for that. Kara had to give herself permission.

_Big boy pants could be so uncomfortable at times._

Winn had nodded encouragingly and gently told her that what she wanted to do about Mon-El was always her choice and he'd be supportive regardless of which direction she chose.

Winn hugged Kara good night and she had whispered her thanks, voice slurred by tears and sleep. Winn smiled and told her _"Anytime, Supergirl"_ and texted Lyra to come home. He and Lyra tucked into bed after Lyra had made a recording of the Supersnoring Kryptonian. _(I'm not passing up blackmail gold over heartbreak. I promise I won't use the footage for at least a year,Winn!)_

They’d woken to breakfast on the table and a far more composed Kara Danvers who calmly announced that She, and the entire Guardian contingency would be meeting up later to formally evict Mon-El from Kara's apartment.

"But pancakes, first!" She crowed.  If Kara hadn't quite hit the cheery tone she was aiming for, Winn and Lyra didn't mention it.

\--

  
Kara had let herself into her apartment with James, Winn, Lucy, Lyra and Maggie following behind her. Lucy had pressed record on her voice memo app before entering the apartment and Maggie, who had shown up to tell Kara Alex was called in for a minor chem explosion in the DEO lab, and had insisted on witnessing _The Douche’s Eviction_ in person, nodded to her approvingly. She had handed her police issue baton to James at the same moment, but Winn figured that if things got violent, Lucy could just delete the evidence. Truth, Justice and the American Way be damned.

Mon-El had been eating Pringles with cream cheese in his boxers on the couch when they'd come in. He'd zeroed in on Lucy and and started spouting things like _defense_ and _nobody said_ and _how long will it be till you can get this ankle bracelet off me?_ _It beeped like crazy when I left the apartment to get cream cheese._  

Lucy had cooly informed him that she was here as Kara’s legal counsel, not his, and that he couldn't afford her for all the money on her planet or his.

Mon-El had been confused and had asked how they planned to get him out of trouble so he could leave the apartment and go back to work. That had been when Kara had snapped and the previous night’s epiphany had poured out of her at top volume.

"Our planets are gone! They're gone and they're never coming back." Mon-El had frozen with a Pringle halfway to his mouth as he processed that Kara was yelling at him. "I told you everything would be new and what was acceptable on Daxam will not be okay on Earth, but you think you can continue acting like a freaking prince and we’ll all make allowances for you when you smile and explain that on Daxam it was different. Newsflash, Mon-El! Earth doesn't care that on Daxam drugs were party appetizers. On Earth drugs are illegal! As a refugee on Earth you need to follow its laws, and you broke them. You broke them by giving horrible drugs to children that made them do horrible things, and that's on you! Not me. You will stand trial for it, or you can take a plea deal if your lawyer can work one out with the DA, but you will face the consequences for your actions!"

Kara had stopped, chest heaving, hands on her hips. Winn had resisted the urge to clap.

Mon-El had started yelling the minute Kara stopped. "That's bull and shit! You’re my girlfriend, you're supposed to help me with my problems!"

Winn had decided it was time to play that asshole. "First of all Mon-El, it's Bullshit, no ‘and’ in the middle. Second," He turned to Kara, "Putting aside the alien and trying to be a hero stuff, when it's just you and him, how does Mon-El make you feel?"

Kara considered the question for a bit, then turned to face Mon-El. Her stance faltered, but her voice didn't. "You make me miserable." She admitted to him. "You use my stuff and don't replace them. You make me pay on dates. You whine about the time I spend with my friends, and whine when we spend time with my friends. You say you should be enough for me and expect me to drop whatever I'm doing when you call."

Mon-El scoffed. "You’re my girlfriend! He repeated. That's what a girlfriend does!"

"No Mon-El." Kara said. "That's what a slave does." She walked across the room and took the Pringles can out of Mon-El’s hand, stood nose to nose with him and continued. "And I, Kara Zor-El, the Last Daughter of Krypton, Girl of Steel and Kara Danvers, Citizen of Earth and Catco reporter, Am. Not. Your. Slave!"

Winn had actually clapped after that. Quietly, though. He’d been impressed, not suicidal.   
Maggie and Lyra had clapped loudly, and James had let out a _Hear, hear!_

Ok, so Winn was a coward. _Fine_. It's not like that wasn't public knowledge anyway.

Mon-El had stomped his foot like a five year old. "I am not going to jail!" He'd roared. "I'm a prince. Princes do not go to jail!"

Lyra had cut in and reeled off an impressive list of Alien princes that had gone to jail for life. Mostly for regicide. Mon-El had gaped at her and blustered, while Maggie videoed the whole exchange on her phone.

Winn had made a mental note to ask for that video while Kara had brought the confrontation to a head. She informed Mon-El that he had three minutes to collect his things and get out of her apartment. She didn't care where he went, or what he did after that. (Which everyone knew to be a lie, but no one had deigned to tell Mon-El that.)

Mon-El had whined that he had no place to go just as Alex walked through the door and let him know that his old cell at the DEO was empty and waiting. J’onn had agreed to keeping him there since Mon-El would have to get used to being behind bars anyway. Mon-El had struck her savagely on the cheek and it became clear that Strategist Alex was in the house as Maggie tossed her still videoing phone to Lyra,read Mon-El his rights, arrested him for assault of a federal agent, and told him to shut the fuck up before she added a resistance charge. Then she declared him a public menace and Alex immediately claimed DEO jurisdiction and carted him off to his new/old cell.

The next day, Winn had asked why she had let him hit her. Alex had grinned even though it caused her half swollen face to shoot needles of pain through her eye sockets. "Because now that son of a bitch doesn't get Netflix" she had told him. Winn had done the cray-cray twirly finger, but Vasquez had taken a break from hacking Algerian bank accounts that were connected to Roulette’s fight club earnings, and leaned over to high five Alex. Alex had high fived Vasquez back and given Winn a noogie.

\--

 

Mon-El’s trial was set for a month later and during that time Kara had practically vanished. She'd show up for Supergirl and Catco duties, but otherwise seemed to have checked out entirely.

Earbuds had been surgically implanted into her ears and her smile had to be coaxed out of her with three times the usual amount of donuts. Alex was beside herself with worry and had gone as far as booking Kara an actual vacation at a Kenyan Elephant Farm before Maggie had put a stop to that by pointing out that it would exceed her credit limit for the month.

Alex canceled the reservation and had spent an hour fretting in a side room, ignoring a major alien rights rally that was taking place downtown in response to the previous weeks human rights rally which had protested alien rights to trial by jury.

Without Alex’s near clairvoyant command of flammable situations, the rally had imploded spectacularly into violence. By Winn’s judgement alien/human cooperation had been set back by ten years minimum. J’onn had been furious and Supergirl was trotted out to give a tiresome press conference on how tragedy helps nothing and nobody. The conference would have been boringly routine if the crowd hadn't spotted the earbud still stuck in her ear, and gone viral with the image, accusing her of disrespecting the real issues humanity faces in light of rising alien illegals on Earth.

Kara had refused to comment on the political quagmire her Supergirl persona was being dragged through when she had returned to the DEO. Instead, she had gone down to see Mon-El for the first time since his incarceration and had come back looking even more devastated then before.

Alex had gone down to beat the shit out of Mon-El and J’onn let her get in a few hits with a lead pipe before calling her off.

That night, Winn had gone to Noonan's, picked out cookie dough and Caramel milk shakes and shown up at L-corp. He'd bribed Jess with the caramel to let him in, and had held Lena's cookie dough shake hostage until she agreed to sit on the couch and hear him out. Lena had told him he had exactly five minutes and had dramatically set a timer because she was Lena-fucking-Luthor and extra that way.

Winn had told her about Kara’s Batman impersonation. "Lena, she's like a different person. She reacts to potstickers like NORMAL people do now! Fix her!" Lena had sighed and dropped down on the couch next to him.

"Does she ever talk to him?" She had asked. Winn, shook his head.

"She did once, but she came back crying and Alex beat him up." Lena had rolled her eyes at Alex’s reaction and then asked what music Kara was into these days.

Winn had face palmed with both hands. "Right! Can't believe I forgot this bit. Lena, she listens to _breakup_ songs! On repeat. Even Taylor Swift ones. The earbuds never come out unless you ask her a direct question. She always seems like she's somewhere else, even when she's right next to you and talking to you."

"Taylor Swift?" Lena had frowned at that. "Serious, then."

Winn had punched Lena in the shoulder. "Seriously, Lena. That's when this gets you worried? When you hear she's been listening to Taylor Swift songs?"

Lena had rolled her eyes again and pressed a button on her desk. Jess had magically appeared in the doorway.

"Perry vs. Swift. Floor is yours." Lena told her with a smirk. Jess had a look on her face that could only be described as gleeful as Winn was forced to suffer through a timeline of some pop star feud that meant nothing to him, but apparently mattered to all millennial girls under 25.

"What would you peg, Kara as?"Lena interrupted Jess’s rambling. Jess had declared Kara a Katy in no uncertain terms. "And if I told you Kara has recently been listening to _Teardrops on My Guitar_?" Lena let the question trail off as Jess’s face twisted into an ‘ _O_ ’of surprise.

Lena nodded, thanked Jess and asked her to email her the minutes of the Maxwell Lord/CFO meeting that haud taken place yesterday. "See," She told Winn triumphantly, "Kara doesn't normally listen to Swift, so it's serious."

Winn had groaned and asked Lena to just give her expert opinion on what was going on with Kara. "

Well, we don't talk much now, but I would say that given what you told me, Kara is going through a Behavioral Self-Blame stage. It's when you take whatever happened thanks to some douche and make yourself crazy reviewing the story for what you could have done differently." Lena's face had been sad and knowing and Winn had understood immediately.

"Yes, I was like that after Lex happened." Lena had ground out. Put your sympathies away, Schott." Winn had held up his hand placatingly, and moved on quickly.

"So, how are you going to get her to snap out of it?" He’d asked.

"Me, why me?" Lena had asked.

"You're her best friend, Lena!" Winn had said exasperated beyond measure. "I don't know what the fuck happened to you two after the whole Mon-El deal went down, but when your name comes up Kara takes the earbuds out voluntarily and that's good enough for me."

Lena buried her face in her hands. "She got scared, Winn. That's what happened. She turned up on my balcony the night after you all threw Mon-El into the DEO basement, and we talked. Then suddenly we were kissing on my couch and then she pushed me away asked for ‘space’ and flew out of my apartment like a demon was after her. So," Lena had shrugged in attempted apathy, "I’ve been giving her space."

Winn stared at her. "Lena Luthor, you're a wuss." He declared and had settled back against the couch and waited.

Lena had spluttered, she had protested, and then capitulated. "Fine! I'm a wuss. I got what I've been dreaming of since she walked into my office," (Winn had mentally fist pumped and reminded himself to collect his $20 from Lucy, James, and Alex.) "And it had to happen in the shittiest circumstances ever. I've been afraid that confronting the issue will cause Kara to bolt, and I'll lose her forever. I can't do that, Winn! I love Kara and the thought of her shutting me out forever is unbearable."

Winn had rolled his eyes so hard they could've scored a strike and proceeded to explain to Lena that when Kara thinks she messed up, she tends to hide out on her couch, eat enough ice cream and Oreos to turn her blood into chocolate raspberry syrup and mope until Alex, or Cat comes to give her kick ass advice. Since Cat was out of town, and Alex hadn't hit the end of her rope yet, it was up to Lena to get her shit together and go talk to Kara.

Lena had whined that she’d rather hold out for Alex. Winn had threatened to change Lena's email address to WussWuthor@L-corp.com. By the time Winn left, he and Lena had role played the expected conversation 20 times, _(Asking Kara if she has feelings for you, and how she wants to move forward with your relationship is not a confrontation with the L-Corp board over canceled scholarship grants. Be Lena, not Miss Luthor!)_ and Winn had a $200 gift card to Game Stop in his pocket. Jess had shoved it at him when he'd walked out of the office.

"Take it and shut it." She'd ordered. So Winn had learned two things that day about Jess: 1. She definitely listens to what goes on in Lena's office. Probably as much for Lena’s safety as it is for her own curiosity. 2. Jess occupies third place on Winn’s list of _**Women-To-Obey-Without-Question.**_

(Top spot belongs to Lyra Strayd, Alex Danvers is a superclose runner-up, then Jess Huang. Fourth is Cat Grant, Fifth is Lucy Lane, and lastly is Red-K Supergirl.)

...

It had taken three days.

On day one Kara had arrived at the DEO in footie pajamas and almost squeezed the geek out of him with a bone crushing hug. "You are an incredible best friend, Winn Schott," She'd whispered in his ear. Then she’d proceeded to find and destroy every stash of Schmurple in the city. She’d found the manufacturing plant (an abandoned warehouse ten miles out of National City and heat visioned it to ash. Then she had come back to the DEO and disappeared into the sparring room with Alex. Every mannequin had been bashed in with a lead pipe.

On day two Lena Luthor showed up at his apartment to ask him how one went about withdrawing from the _We-Like-Kara-Danvers- and-She-Likes-Us-But-not-Like-That Club_. Winn had conferred with James and decided that if resignation was tendered with a genuine promise to be good to Kara, Lena would always be welcome to come car bashing with them. Lyra had come up behind him as he’d laughingly waved Lena out the door and wrapped her arms around his waist. "You’re a really great friend, Winn Schott." She’d whispered in his ear.

On day three Kara had stood next to National City’s Mayor, in full super gear, as the District Attorney credited final arrests to Supergirl and reeled off a list of names connected to Shmurple and announced that all would be tried for illegal drug manufacturing and distribution.

  
After the press conference was done, Kara had gotten into civilian clothes and dragged them all to the Alien bar. Something about new memories needing to be made.

Lena had shown up at the bar forty minutes after everyone else and Alex had taken one look at Kara’s face and asked her who the smile was for. "You’re wearing the James Smile, Kara, but James is over there photographing Lucy getting blind drunk while arm wrestling a Narlak, so who’s the smile for?"

"That would be me," Lena said with a small smile at Alex. "I'm the new James." Alex had stared and Kara had slid an arm around Lena’s waist.

"You hurt her, Luthor, and there’s another cell in the DEO with your name on it." Alex promised fiercely.

"I hurt her and I’ll walk into the cell voluntarily." Lena told her solemnly. Kara had done the whole giggle routine of protest and Alex had grinned and everyone relaxed. Then everyone got blind drunk and Winn woke up the next morning with Lyra next to him in bed, and a bottle of water and aspirin on the bed table.

He couldn’t remember much of what happened after 1 am, but he could remember the highlights.

A blurted " _Marry Me?"_ From Alex after Maggie handed her a drink refill had accidentally turned into an actual proposal. He couldn’t remember if Maggie said yes. Kara and Lena had gotten themselves cut off and thrown out after M’gann found them doing _Winn does NOT want to know_ in the alley way, and Lucy and James had beat the entire bar at pool and won free shots forever. Pool badassery got serious respect in the Alien world.

Most of all, Winn thought he remembered a moment on the dance floor when Lyra had deftly spun away from and then into him, and held up two tickets to the Metrpolis Gamer Association Convention. The " _I love you, so much_." Had slipped out unbidden and Lyra had laughed, kissed him on the mouth and told him, _"I love_ _you too, Winn Schott."_

So, Winn Schott, Ladies and Gents: Thinks Kara Danvers is kind, passionate and beautiful and he is lucky to have her as a best friend. His best friend’s girlfriend, Lena Luthor is his partner in crime when it comes to refining his nerdy, techie gamer skills and is advising him on exactly how much it’s ok to charge the US army for his Undefeatable Telelens. ("Way more, Mr. Schott. Way more. Also, we’re not calling it that.") He’s learned that sometimes, in very rare instances, it’s ok to be that asshole. He also needs to put his mad sewing skills to use, pronto, cuz he needs his big boy pants in a size up now. As for never getting the girl? You know what they say – _keep car bashing and never say never_.   
  
Oh, wait. Scary Alex says that.

**Notes for the Chapter:**

> I like my ramble. Let me know if you did too. 
> 
> This was finished after I saw s/t online about Winn going dark in S3. I wanted to keep the sunshine and happiness on him for as long as possible.

**Author's Note:**

> This is rambly and grammar errors are abundant. Posting from my phone and will edit when I get to a computer. :)  
> This fic was inspired by Maren Morris's 'Hero' album, especially the tracks, 'Rich' and 'Drunk Girls Don't Cry'.


End file.
